US4374769A - Water-soluble tris phenyl bisazo dyes for polyamide fibers - Google Patents
Water-soluble tris phenyl bisazo dyes for polyamide fibers Download PDFInfo
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- US4374769A US4374769A US06/274,599 US27459981A US4374769A US 4374769 A US4374769 A US 4374769A US 27459981 A US27459981 A US 27459981A US 4374769 A US4374769 A US 4374769A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/062—Phenols
- C09B31/065—Phenols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
- C09B31/047—Amino-benzenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
- C09B62/66—Azo dyes
- C09B62/67—Disazo or polyazo dyes
Definitions
- bisazo dyes bearing one or two sulfated alkoxycarbonyl or sulfated alkylcarbamyl groups. These dyes are water-soluble exhibiting excellent dyeing properties on polyamide fibers and also are useful for dyeing cellulose acetate and wool.
- the dyes have the general formula: ##STR2## wherein X is --O--, --NH--, --N(alkyl)--, or --N(aryl)--; Z is selected from straight or branched-chain alkylene, and such alkylene containing one or two internal linkages independently selected from ether, amine and amide; M is H, Na, K, or NH 4 ; n is 1 or 2; R 3 is --OH, alkoxy or --NR 8 R 9 wherein R 8 and R 9 are independently selected from H and alkyl and when either R 4 or R 5 is hydroxy or alkoxy ortho to the azo radical, R 3 is further selected from hydrogen, halogen, alkyl, aryl and acylamido; and R, R 1 , R 2 , R 4 , and R 5 are the same or different groups selected from hydrogen, halogen, hydroxyl, alkyl, aryl, alkoxy, and acylamido, with the proviso that when R 3 is neither
- alkyl, alkylene, alkoxy and aryl moieties may be substituted with one to three substituents selected from hydroxy, halogen, cyano, succinimido, cyclohexyl, alkylsulfonyl, alkylthio, alkanoyl, alkanoyloxy, amino, alkylamino, dialkyl-amino, arylamino, furyl, alkoxy, phenoxy, alkanoylamino, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, phenyl and phenyl substituted with alkyl, alkoxy, halogen, alkanoyl-amino, cyano or alkoxycarbonyl, --COOR 6 wherein R 6 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulf
- These dyes impart yellow to red shades to fibers, particularly polyamides, and are especially useful for dyeing polyamide (nylon) carpets, generally giving good fastness to light, ozone, oxides of nitrogen, washing, sublimation, crocking, and the like, and having good leveling, exhaustion, build properties, and stability to variations in dyeing condition such as pH and temperature.
- the dyes bearing sulfated alkylcarbamyl groups may be prepared by reacting a diazotizable coupler (B--NH 2 ) with the diazonium salt of a benzene compound (ring A) which contains one or two carbalkoxy groups.
- ring A diazotizable coupler
- the resulting monoazo dye A--N ⁇ N--B--NH 2 is diazotized and coupled with an ortho or para-coupling moiety such as a phenol (C--OH).
- the phenolic group on ring C may be treated subsequently, for example, with an alkyl halide or dialkyl sulfate to alkylate the phenolic group of ring C.
- the dyes bearing sulfated alkoxycarbonyl groups are prepared, for example, from an aniline compound (A--NH 2 ) containing one or two hydroxyalkoxy carbonyl groups.
- A--NH 2 aniline compound
- the aniline compound is diazotized, coupled with B--NH 2 , diazotized again, then coupled with C--OH and, if desired, alkylated on the phenolic group of the third ring.
- Reaction with concentrated sulfuric acid to form the sulfate of the hydroxyalkoxy carbonyl group may be performed either before the first diazotization or at any time thereafter.
- the dyes are customarily isolated in the form of the alkali salt.
- Methyl anthranilate (30.23 g) is diazotized at 0°-2° C. by dissolving it in dilute hydrochloric acid (60 ml of 37% HCl in 200 ml of water) and adding sufficient sodium nitrite solution (14.4 g of NaNO 2 in 40 ml of water) to the anthranilate solution over a period of 45-50 minutes.
- the diazotized material preferably is allowed to stand at about 2° C. for one-half hour longer before being used.
- a coupler solution consisting of 2.82 g of phenol dissolved in 100 ml of water containing 4.38 g of 98% sodium hydroxide is cooled with ice to maintain a temperature of about 0° C., and the above diazonium solution added thereto to bring the total volume to about 400 ml.
- the product solidifies over night and is readily filterable.
- the ⁇ max. in acetone is at 405 nm. and the product is 4'-[(2"-carbomethoxyphenyl)azo]-5'-methyl-2'-methoxy-4-hydroxy-azo-benzene.
- Example 2 A 4.00 g portion of the product of Example 2 is added to a solution of 10 ml of ethanolamine and 5 ml of isopropanol. The solution is heated by steam for 40 minutes and poured into a solution of 10 ml of acetic acid in 30 ml of water and the product was removed by filtration. Recrystallization is from hot, dilute isopropanol to remove some unreacted material. The ⁇ max. in acetone is at 418 nm. The product is the disperse dye 4'-[(2"-N-hydroxyethylcarbamylphenyl)-azo]-5'-methyl-2'-methoxy-4-hydroxy-azo-benzene.
- Example 3 The product of Example 3 is sulfated in concentrated sulfuric acid, using 2.00 g of intermediate for 10 ml of sulfuric acid, and using a bath of ice water to prevent overheating. The solution is added to about 35 g of ice and the precipitate removed by filtration, slurried in cold water, and refiltered. The wet precipitate is treated with dilute sodium hydroxide solution until soluble, then with acetic acid until reprecipitated at about pH 6. The product is removed by filtration and dried at 60° C. The product is 4'-[(2"-N-sulfatoethyl-carbamylphenyl)azo]-5'-methyl-2'-methoxy-4-hydroxy-azobenzene, Na salt. The ⁇ max. in aqueous acetone is at 522 nm. and the acid dye is yellow-orange with good properties on nylon 6 tricot fabric and nylon 6.6 carpet.
- Example 3 Approximately one gram of the product of Example 3 is treated in basic solution (25 ml) with about five grams of diethyl sulfate at 80°-90° C.
- the basic solution is made from 5 g of soldium bicarbonate in 100 ml of water, with sufficient 25% sodium hydroxide solution to increase the pH to about 11.
- the diethyl sulfate is added dropwise during about two hours, along with sufficient 25% sodium hydroxide solution to maintain the pH at 11.
- the product is recovered by filtration after dilution of the reaction system with water and cooling with ice.
- the product consists of the disperse dye 4'-[(2"-N-hydroxyethylcarbamyl-phenyl)azo]-2'-methyl-2'-methoxy-4-ethoxy-azobenzene, having ⁇ max. in acetone at 408 mm.
- Example 5 About one-third gram of the product of Example 5 is dissolved in just enough concentrated sulfuric acid (2-3 ml) to dissolve it readily at room temperature. The solution is added to sufficient ice to keep the temperature below 20° C. as the solution is made basic with sodium hydroxide solution. The product is removed by filtration and washed with 15% sodium sulfate solution.
- the product is the acid dye 4'[(2"-N-sulfoethylcarbamylphenyl)azo]-5'-methyl-2'-methoxy-4-ethoxy-azo-benzene, Na salt having a ⁇ max. at 413 nm and thus imparting to nylon fibers an orange shade less reddish than the dye of Example 4.
- the dye exhibits good properties such as lightfastness on both nylon 6 tricot fabric and nylon 6.6 carpet and shows good exhaustion, build, and migration on nylon carpet.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Coloring (AREA)
Abstract
Description
__________________________________________________________________________ ##STR4##
__________________________________________________________________________ Ex. No. XZ M R R.sub.1 R.sub.2 __________________________________________________________________________ 7 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na H H H 8 NHCH.sub.2 CH.sub.2 Na H H H 9 NHCH.sub.2 CH.sub.2 Na H H H 10 NHCH.sub.2 CH.sub.2 Na H H H 11 NHCH.sub.2 CH.sub.2 K H H H 12 NHCH.sub.2 CH.sub.2 K H 3'-CH.sub.3 5'-CH.sub.3 13 NHCH.sub.2 CH.sub.2 Na H H H 14 N(CH.sub.3)CH.sub.2 CH.sub.2 Na 4"-Br H H 15 OCH.sub.2 CH.sub.2 Na H H H 16 NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na 4"-Cl H H 17 NHCH.sub.2 CH.sub.2 Na H H 5'-NHCOCH.sub.3 18 NHCH.sub.2 CH.sub.2 Na H H 5'-NHCOCH.sub.3 19 NHCH.sub.2 CH.sub.2 K 4"-OH 2'-Cl H 20 NHCH.sub.2 CH.sub.2 K H 2'-Cl H 21 NHCH.sub.2 CH.sub.2 Na H 3'-CH.sub.3 H 22 NHCH.sub.2 CH.sub.2 Na H 3'-CH.sub.3 H 23 NHCH.sub.2 CH.sub.2 Na H 3'-CH.sub.3 H 24 NHCH.sub.2 CH.sub.2 Na 6"-Br 3'-CH.sub.3 H 25 NHCH.sub.2 CH.sub.2 Na 6"-Br 3'-CH.sub.3 H 26 NHCH.sub.2 CH.sub.2 Na H 3'-CH.sub.3 H 27 NHC.sub.2 H.sub.4 NHC.sub.2 H.sub.4 K H 3'-CH.sub.3 H 28 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na H 3'-CH.sub.3 H 29 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na H H H 30 NHCH.sub.2 CH(CH.sub.3)CH.sub.2 Na H 3'-OCH.sub.3 H 31 NHCH.sub.2 CH.sub.2 Na H 3'-OCH.sub.3 H 32 OCH.sub.2 CHClCH.sub.2 K 5"-Br 3'-OCH.sub.3 H 33 NHCH.sub.2 CH.sub.2 K H 3'-OCH.sub.3 H 34 OCH.sub.2 CH.sub.2 NH.sub.4 H 3'-OCH.sub.3 H 35 NHCH.sub.2 CH.sub.2 Na H 3'-OC.sub.2 H.sub.5 H 36 NHCH.sub.2 CH.sub.2 Na H 3'-NHCOCH.sub.3 H 37 NHCH.sub.2 CH.sub.2 Na 6"-Cl 2'-Br 5'-Br 38 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 39 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 40 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 41 NHC.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 NH.sub.4 4"-Br 2'-CH.sub.3 5'-CH.sub.3 42 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 43 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 44 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 45 NHCH.sub.2 CH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 46 NHCH.sub.2 CH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 47 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-CH.sub.3 48 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-OCH.sub.3 49 OCH.sub.2 CH.sub.2 NH.sub.4 H 2'-CH.sub.3 5'-OCH.sub.3 50 NHCH.sub.2 CH.sub.2 K H 2'-CH.sub.3 5'-OCH.sub.3 51 NHCH.sub.2 CH.sub.2 K H 2'-CH.sub.3 5'-NHCOCH.sub.3 52 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.3 5'-NHCOCH.sub.3 53 NHCH.sub.2 CH.sub.2 Na H 2'-OCH.sub.3 5'-OCH.sub.3 54 NHCH.sub.2 CH.sub.2 Na H 2'-OCH.sub.3 5'-OCH.sub.3 55 OCH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 Na H 2'-OCH.sub.3 5'-OCH.sub.3 56 NHCH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 NH.sub.4 H 2'-OCH.sub.3 5'-OCH.sub.3 57 NHCH.sub.2 CHCl Na H H H 58 NHCH.sub.2 CHCl Na H H 5'-C.sub.2 H.sub.4 CN 59 NHCH.sub.2 CHCl K H H H 60 NHCH.sub.2 CHCl K H 3'-OH 5'-OH 61 OCH.sub.2 CH.sub.2 K H 3'-CH.sub.2 C.sub.6 H.sub.5 H 62 NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 K 4"-Cl H H 63 NHCH(C.sub.6 H.sub.11)CH.sub.2 K H H 5'-NHCOCH.sub.3 64 NHCH.sub.2 CH.sub.2 K 4"-OH 2'-Cl H 65 NHCH.sub.2 CH.sub.2 Na H 3'-CH.sub.2 Cl H 66 NHCH.sub.2 CH.sub.2 Na H 3'-CH.sub.2 Cl 5'-OCH.sub.2 Br 67 NHCH.sub.2 CH.sub.2 Na H 3'-CH.sub.2 Cl H 68 NHCH.sub.2 CH.sub.2 Na 6"-Br 3'-CH.sub.2 CN H 69 NHCH.sub.2 CH.sub.2 Na 6"-Br 3'-CH.sub.3 H 70 NHCH.sub.2 CH.sub.2 Na H 3'-CH.sub.3 H 71 NHC.sub.2 H.sub.4 NHC.sub.2 H.sub.4 K 4"-C.sub.2 H.sub.5 3'-CH.sub.3 H 72 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na H 3'-CH.sub.2 OH H 73 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na H H H 74 NHCH.sub.2 CH(CH.sub.3)CH.sub.2 Na H 3'-OCH.sub.3 H 75 NHCHClCH.sub.2 Na H 3'-OCH.sub.3 H 76 NHCH.sub.2 CH.sub.2 Na 5"-OCH.sub.3 3'-OCH.sub.3 H 77 NHCH.sub.2 CH.sub.2 Na H 2'-CH.sub.2 OC.sub.2 H.sub.5 5'-CH.sub.3 78 NHC.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 NH.sub.4 4'-Br H 5'-CH.sub.3 79 NHCH(C.sub.6 H.sub.5)CH.sub.2 K H H 5'-CH.sub.3 80 NHCH.sub.2 CH.sub.2 K H H 5'-NHCOCH.sub.3 81 NHCH.sub.2 CH.sub.2 Na H H 5'-NHCOCH.sub.3 82 NHCH.sub.2 CH.sub.2 Na H 2'-OCH.sub.3 5'-OCH.sub.2 COOCH.sub.3 __________________________________________________________________________ Ex. No. R.sub.3 R.sub.4 R.sub.5 __________________________________________________________________________ 7 OH H H 8 OCH.sub.3 5-CH.sub.3 H 9 OC.sub.2 H.sub.5 5-CH.sub.3 H 10 OH 2-CH.sub.3 H 11 OH 5-CH.sub.3 H 12 OH H H 13 OH 3-CH.sub.3 H 14 OH 5-C.sub.2 H.sub.5 H 15 OH 2-CH.sub.3 H 16 OH H 5-OH 17 OH H H 18 OC.sub.2 H.sub.5 H H 19 OH H H 20 OH 2-C.sub.2 H.sub.5 H 21 OH H H 22 OH 2-Cl H 23 OC.sub.2 H.sub.5 2-Cl H 24 OC.sub.2 H.sub.5 2-OH H 25 OC.sub.2 H.sub.5 3-CH.sub.3 H 26 H 2-CH.sub.3 6-OCH.sub.3 27 H 2-OCH.sub.3 5-CH.sub.3 28 OC.sub.2 H.sub.5 3-CH.sub.3 5-CH.sub.3 29 OH 2-CH.sub.3 6-CH.sub.3 30 OH 2-C.sub.2 H.sub.5 H 31 OH H H 32 OC.sub.2 H.sub.5 2-CH.sub.3 H 33 OC.sub.2 H.sub.5 2-OCH.sub.3 H 34 OC.sub.2 H.sub.5 2-Cl H 35 OC.sub.2 H.sub.5 2-CH.sub.3 6-CH.sub.3 36 OC.sub.2 H.sub.5 2-CH.sub.3 H 37 OC.sub.2 H.sub.5 H H 38 OCH.sub.3 H H 39 OCH.sub.3 3-CH.sub.3 H 40 OCH.sub.3 2-CH.sub.3 H 41 OCH.sub.3 2-CH.sub.3 6-CH.sub.3 42 OCH.sub.3 2-CH.sub.3 5-CH.sub.3 43 OCH.sub.3 3-CH.sub.3 5-CH.sub.3 44 OH 3-CH.sub.3 5-CH.sub.3 45 OH 2-CH.sub.3 H 46 OH 2-CH.sub.3 6-CH.sub.3 47 OH 2-CH.sub.3 5-CH.sub.3 48 OH H H 49 OC.sub.2 H.sub.5 H H 50 OCH.sub.3 H H 51 OH 2-CH.sub.3 6-CH.sub.3 52 OH 2-CH.sub.3 6-CH.sub.3 53 OH 5-CH.sub.3 H 54 OH 2-Cl H 55 OH 2-CH.sub.3 6-CH.sub.3 56 OH 3-CH.sub.3 5-CH.sub.3 57 OCH.sub.2 Cl 5-CH.sub.3 H 58 OC.sub.2 H.sub.5 5-CH.sub.3 H 59 OH 5-CH.sub.2 Cl H 60 OH H H 61 OH 2-CH.sub.3 H 62 OH H 5-OH 63 OH H H 64 OH H 5-C.sub.2 H.sub.4 OCOCH.sub.3 65 OH H H 66 OH 2-Cl H 67 OC.sub.2 H.sub.4 C.sub.6 H.sub.11 2-Cl H 68 OC.sub.2 H.sub.4 C.sub.6 H.sub.11 2-OH H 69 OC.sub.2 H.sub.4 C.sub.6 H.sub.11 3-CH.sub.3 H 70 H 2-OCH.sub.3 6-CH.sub.2 Cl 71 H 2-OCH.sub.3 5-CH.sub.3 72 OC.sub.2 H.sub.5 3-CH.sub.3 5-CH.sub.3 73 OH 2-CH.sub.2 CN 6-CH.sub.3 74 OH 2-C.sub.2 H.sub.4 OC.sub.2 H.sub.5 H 75 OH H H 76 OH 2-OCH.sub.3 H 77 OCH.sub.3 H H 78 OC.sub.2 H.sub.4 OCH.sub.3 H 6-CH.sub.3 79 OCH.sub.3 H H 80 OH 2-C.sub.2 H.sub.4 OCH.sub.3 6-CH.sub.3 81 OH 2-C.sub.2 H.sub.4 OC.sub.2 H.sub.5 6-CH.sub.3 82 OH 5-CH.sub.3 H __________________________________________________________________________
__________________________________________________________________________ 83 --OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 -- K H H H --OH H H 84 --NHCH.sub.2 CH.sub.2 -- Na H H H --OH 3-C.sub.2 H.sub.5 H 85 --NHCH.sub.2 CH.sub.2 -- Na H H 5'-NHCOCH.sub.3 --OC.sub.2 H.sub.5 H H 86 --NHCH.sub.2 CH.sub.2 -- Na H 3'-CH.sub.3 H --OH H H 87 --NHCH.sub.2 CH.sub.2 -- Na 4"-Cl 3'-OCH.sub.3 H --OC.sub.2 H.sub.5 H H 88 --NHCH.sub.2 CH.sub.2 -- Na H 2'-OCH.sub.3 5'-OCH.sub.3 --OH 5-CH.sub.3 H __________________________________________________________________________
__________________________________________________________________________ 89 --NHCH.sub.2 CH.sub.2 -- K 2"-Br 2'-CH.sub.3 5'-CH.sub.3 --OC.sub.2 H.sub.5 H H 90 --NHCH.sub.2 CH.sub.2 -- Na H 2'-CH.sub.3 5'-CH.sub.3 --OC.sub.2 H.sub.5 2-Cl H 91 --NHCH.sub.2 CH.sub.2 -- Na H 2'-CH.sub.3 5'-CH.sub.3 --OC.sub.2 H.sub.5 3-CH.sub.3 5-CH.sub.3 92 --OCH.sub.2 CH.sub.2 -- Na H 2'-Br 5'-Br --OH H H 93 --NHCH.sub.2 CH.sub.2 CH.sub.2 -- NH.sub.4 3"-Br 3'-OCH.sub.3 H --OH 2-CH.sub.3 5-CH.sub.3 94 --OCH.sub.2 CH(OSO.sub.3 Na)CH.sub.2 -- Na H 3'-OCH.sub.3 H --OH 3-CH.sub.3 5-CH.sub.3 95 --NHCH.sub.2 CH.sub.2 -- Na H 2'-OCH.sub.3 5'-CH.sub.3 --OCH.sub.3 H H 96 --NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 -- K H 2'-OCH.sub.3 5'-CH.sub.3 --OC.sub.2 H.sub.5 H H __________________________________________________________________________
__________________________________________________________________________ 97 --NHCH.sub.2 CH.sub.2 -- Na H 2'-OCH.sub.3 5'-CH.sub.3 --OH H H 98 --NHCH.sub.2 CH.sub.2 -- Na H 2'-OCH.sub.3 5'-CH.sub.3 --OCH(CH.sub.3).sub.2 H H 99 --NHCH.sub.2 CH.sub.2 -- Na H 3'-CH.sub.3 H --OH H H 100 --NHCH.sub.2 CH.sub.2 CH.sub.2 -- Na H 3'-CH.sub.3 H --OCH.sub.3 2-CH.sub.3 H 101 --OCH.sub.2 CH.sub.2 -- Na H 2'-CH.sub.3 5'-CH.sub.3 --OC.sub.2 H.sub.5 H H __________________________________________________________________________
__________________________________________________________________________ 102 --NHCH.sub.2 CH.sub.2 -- Na H H H --OH H H 103 --NHCH.sub.2 CH.sub.2 -- Na H H H --OC.sub.2 H.sub.5 H H 104 --NHCH.sub.2 CH.sub.2 -- K H 3'-CH.sub.3 H --OH H H 105 --NHCH.sub.2 CH.sub.2 -- NH.sub.4 H 3'-CH.sub.3 H --OC.sub.2 H.sub.5 H H 106 --OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 -- Na H 3'-OCH.sub.3 H --OCH.sub.3 5-CH.sub.3 H __________________________________________________________________________
__________________________________________________________________________ 107 --OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na H H H --NH.sub.2 H H 108 --NHCH.sub.2 CH.sub.2 -- Na H H H --NHC.sub.2 H.sub.5 2-CH.sub.3 H 109 --NHCH.sub.2 CH.sub.2 -- Na H H H --N(C.sub.2 H.sub.5).sub.2 2-CH.sub.3 H 110 --NHCH.sub.2 CH.sub.2 -- Na H H H --NHC.sub.2 H.sub.4 OH 2-CH.sub.3 H 111 --NHCH.sub.2 CH.sub.2 -- K H H H --N(CH.sub.2 CH.sub.2 Cl).sub.2 2-CH.sub.3 H 112 --NHCH.sub.2 CH.sub.2 -- K H 3'-OH 5'-OH --NHCH.sub.2 CH.sub.2 C.sub.6 H.sub.5 OCH.sub.3 H 113 --NHCH.sub.2 CH.sub.2 -- Na H H H --N(C.sub.2 H.sub.5).sub.2 NHCOCH.sub.3 H 114 --N(CH.sub.3)CH.sub.2 CH.sub.2 -- Na 4"-Br H H --N(C.sub.2 H.sub.5).sub.2 Cl H 115 --OCH.sub.2 CH.sub.2 -- Na H H H -- N(C.sub.2 H.sub.5).sub.2 2-CH.sub.3 5-CH.sub.3 116 --NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 -- Na 4"-Cl H H --N(C.sub.2 H.sub.5).sub.2 2-C.sub.2 H.sub.5 5-CH.sub.3 117 --NHCH.sub.2 CH.sub.2 -- Na H H 5'-NHCOCH.sub.3 --N(C.sub.2 H.sub.5).sub.2 2-Cl 5-CH.sub.3 118 --NHCH.sub.2 CH.sub.2 -- Na H H 5'-NHCOCH.sub.3 --N(C.sub.2 H.sub.5).sub.2 2-CH.sub.3 5-OCH.sub.3 119 --NHCH.sub.2 CH.sub.2 K 4"-OH 2'-Cl H --N(C.sub.2 H.sub.5).sub.2 2-NHCOCH.sub.3 5-CH.sub.3 120 --NHCH.sub.2 CH.sub.2 -- K H 2'-Cl H --NHC.sub.2 H.sub.5 2-NHCOCH.sub.3 5-CH.sub.3 121 --NHCH.sub.2 CH.sub.2 -- Na H 3'-CH.sub.3 H --NHC.sub.4 H.sub.9 --n 2-CH.sub.3 5-OCH.sub.3 122 --NHCH.sub.2 CH.sub.2 -- Na H 3'-CH.sub.3 H --NHCH.sub.3 2-NHCOCH.sub.3 5-CH.sub.3 __________________________________________________________________________
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/274,599 US4374769A (en) | 1981-06-17 | 1981-06-17 | Water-soluble tris phenyl bisazo dyes for polyamide fibers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/274,599 US4374769A (en) | 1981-06-17 | 1981-06-17 | Water-soluble tris phenyl bisazo dyes for polyamide fibers |
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Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2265425A (en) * | 1938-10-24 | 1941-12-09 | Gen Aniline & Film Corp | Disazo dyestuffs |
US2670265A (en) * | 1954-02-23 | Process | ||
US2720518A (en) * | 1950-08-01 | 1955-10-11 | Ciba Ltd | Azo-dyestuffs |
US2773863A (en) * | 1953-01-28 | 1956-12-11 | Ciba Ltd | Monoazo-dyestuffs |
US2790172A (en) * | 1955-09-08 | 1957-04-23 | Gen Aniline & Film Corp | Heterocyclic fused ring phenols |
US3114754A (en) * | 1959-10-12 | 1963-12-17 | Ici Ltd | Azo, anthraquinone, nitro, and phthalocyanine dyestuffs having beta-acyloxyethyl sulphonyl or an nu-(beta-acyloxyethyl) sulfamyl radical |
US3232927A (en) * | 1962-12-31 | 1966-02-01 | Gen Aniline & Film Corp | Water soluble organic dyestuffs |
US3531459A (en) * | 1964-12-02 | 1970-09-29 | Gen Aniline & Film Corp | Monoazo-dyestuffs containing fiber-reactive and water solubilizing radicals |
US3957751A (en) * | 1972-01-12 | 1976-05-18 | Hoechst Aktiengesellschaft | Water-soluble reactive dyestuffs of the monoazo series containing an active methylene coupling component |
US3998805A (en) * | 1973-04-04 | 1976-12-21 | Ciba-Geigy Corporation | Sulphatoethylene (sulphonyl or sulphonylamino) phenyleneazo dyestuffs |
US4036824A (en) * | 1969-12-04 | 1977-07-19 | Bayer Aktiengesellschaft | Disazo dyestuffs containing A-O-alkylene-O-SO3 H group |
US4119623A (en) * | 1975-08-16 | 1978-10-10 | Bayer Aktiengesellschaft | Water-soluble diphenylamine-azo-sulfatoalkoxyphenyl dyestuffs |
US4301068A (en) * | 1979-12-05 | 1981-11-17 | Eastman Kodak Company | Azo dyes from a 2-aminothiophene having 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydrocyalkyl) carbamoyl groups on its ring |
-
1981
- 1981-06-17 US US06/274,599 patent/US4374769A/en not_active Expired - Fee Related
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2670265A (en) * | 1954-02-23 | Process | ||
US2265425A (en) * | 1938-10-24 | 1941-12-09 | Gen Aniline & Film Corp | Disazo dyestuffs |
US2720518A (en) * | 1950-08-01 | 1955-10-11 | Ciba Ltd | Azo-dyestuffs |
US2773863A (en) * | 1953-01-28 | 1956-12-11 | Ciba Ltd | Monoazo-dyestuffs |
US2790172A (en) * | 1955-09-08 | 1957-04-23 | Gen Aniline & Film Corp | Heterocyclic fused ring phenols |
US3114754A (en) * | 1959-10-12 | 1963-12-17 | Ici Ltd | Azo, anthraquinone, nitro, and phthalocyanine dyestuffs having beta-acyloxyethyl sulphonyl or an nu-(beta-acyloxyethyl) sulfamyl radical |
US3232927A (en) * | 1962-12-31 | 1966-02-01 | Gen Aniline & Film Corp | Water soluble organic dyestuffs |
US3531459A (en) * | 1964-12-02 | 1970-09-29 | Gen Aniline & Film Corp | Monoazo-dyestuffs containing fiber-reactive and water solubilizing radicals |
US4036824A (en) * | 1969-12-04 | 1977-07-19 | Bayer Aktiengesellschaft | Disazo dyestuffs containing A-O-alkylene-O-SO3 H group |
US3957751A (en) * | 1972-01-12 | 1976-05-18 | Hoechst Aktiengesellschaft | Water-soluble reactive dyestuffs of the monoazo series containing an active methylene coupling component |
US3998805A (en) * | 1973-04-04 | 1976-12-21 | Ciba-Geigy Corporation | Sulphatoethylene (sulphonyl or sulphonylamino) phenyleneazo dyestuffs |
US4119623A (en) * | 1975-08-16 | 1978-10-10 | Bayer Aktiengesellschaft | Water-soluble diphenylamine-azo-sulfatoalkoxyphenyl dyestuffs |
US4301068A (en) * | 1979-12-05 | 1981-11-17 | Eastman Kodak Company | Azo dyes from a 2-aminothiophene having 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydrocyalkyl) carbamoyl groups on its ring |
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